(Phenylmethyl)hydrazine → 2'-benzyl-2(R)-[4-cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbonyl]butyl]-2'-[2-(1,2,3-triazol-1-yl)acetyl]valerohydrazide

HRID 1979226Notes

Reaction equation

HRID 1979226 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:22][CH:23]([CH3:25])C)[C:19]([OH:21])=O)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:7])([CH3:4])(C)C.[CH2:26]([NH:33][NH2:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[N:35]1([CH2:40][C:41]([OH:43])=O)[CH:39]=[CH:38][N:37]=[N:36]1>>[CH2:26]([N:33]([C:41](=[O:43])[CH2:40][N:35]1[CH:39]=[CH:38][N:37]=[N:36]1)[NH:34][C:19](=[O:21])[C@@H:18]([C@@H:8]([C:6]([O:5][CH:1]1[CH2:4][CH2:9][CH2:8][CH2:6][O:5]1)=[O:7])[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[CH2:22][CH2:23][CH3:25])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 11157(Phenylmethyl)hydrazineHCID 190184992-(1H-1,2,3-triazol-1-yl)acetic acidHCID 206580082(R)-[1(S)-(tert-butoxycarbonyl)-4-cyclohexylbutyl]-4-methylvaleric acid

Product 1

HCID 699537452'-benzyl-2(R)-[4-cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbonyl]butyl]-2'-[2-(1,2,3-triazol-1-yl)acetyl]valerohydrazide

Procedure

In a manner analogous to that described in Example 1, parts (iii)-(vii) and Example 8, from 2(R)-[1(S)-(tert-butoxycarbonyl)-4-cyclohexylbutyl]-4-methylvaleric acid and benzylhydrazine and using 1,2,3-triazole-1-acetic acid in place of N-tert.butoxycarbonyl-β-alanine in Example 8, there was obtained 2′-benzyl-2(R)-[4-cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbonyl]butyl]-2′-[2-(1,2,3-triazol-1-yl)acetyl]valerohydrazide in the form of a white solid.

Sources & evidence

ORD record
ord-ba1608ca534a4e3cb61fd227e5b8cd57
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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